4. Jacob (A Simple Plan)

If you want to be deeply impressed by a crime movie and then feel depressed for days afterwards, watch Sam Raimi’s A Simple Plan. It’s the tale of a few sad n’ lost country boys who find a bag of stolen drug money in the woods, decide to keep it, and then watch their lives slowly fall apart. Everyone is sad in the move, but no one more so than Billy Bob Thorton’s Jacob. He’s a man with some unnamed mental condition who seems trapped in a perpetual adolescence. It’s like watching a child in a man’s body, but not even a happy child. More like that kid you felt sorry for in Grade 3. When he eventually starts killing for greed, Thorton’s character becomes one of the saddest to ever appear in a movie. It’s one of the actor’s greatest performance and easily one of the most pathetic criminals in the history of films.